Hydrochloric Acid → 3-Chloro-4-cyclohexylcinnamic acid

HRID 26562

Reaction equation

HRID 26562 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH:5]=O.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1.Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH:5]=[CH:17][C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic Acid2×HCID 8082PiperidineHCID 107277773-Chloro-4-cyclohexylbenzaldehyde

Product 1

HCID 542933553-Chloro-4-cyclohexylcinnamic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Chloro-4-cyclohexylbenzaldehyde (0.1 mole), malonic acid (0.2 moles), and dry pyridine (175 ml) are placed in a 1 l round-bottom flask. The malonic acid is dissolved by shaking on a steam bath and piperidine (0.5 ml) is added. The reaction is allowed to take place on the steam bath for 4 hours. After standing at room temperature overnight, the mixture is refluxed for 1 hour and cooled. The reaction mixture is poured into 250 ml of ice water and acidified with concentrated hydrochloric acid (80 ml) with stirring. The crystals of product are collected by filtration, washed with water (4× 150 ml) and air dried. Recrystallization from acetone-water gives 3-chloro-4-cyclohexylcinnamic acid.

Workup

  1. customfor 4 hours
  2. temperaturethe mixture is refluxed for 1 hour
  3. temperaturecooled
  4. stirringwith stirring
  5. filtrationThe crystals of product are collected by filtration
  6. washwashed with water (4× 150 ml) and air
  7. customdried
  8. customRecrystallization from acetone-water

Sources & evidence

ORD record
ord-3d9256a617834f628b42d114deddc829
Source dataset
uspto-grants-1979_04
Patent number
US04150148

Linked notes

Loading…